EP0056500A2 - 2,2-Dimethyl-propionic acid esters, their use as perfuming agents and composition containing one of them - Google Patents

2,2-Dimethyl-propionic acid esters, their use as perfuming agents and composition containing one of them Download PDF

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Publication number
EP0056500A2
EP0056500A2 EP81201262A EP81201262A EP0056500A2 EP 0056500 A2 EP0056500 A2 EP 0056500A2 EP 81201262 A EP81201262 A EP 81201262A EP 81201262 A EP81201262 A EP 81201262A EP 0056500 A2 EP0056500 A2 EP 0056500A2
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Prior art keywords
formula
pivalate
perfuming
acid esters
compounds
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German (de)
French (fr)
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EP0056500A3 (en
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Dietrich Kastner
Erling Sundt
Roger Chappaz
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Firmenich SA
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Firmenich SA
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring

Definitions

  • the invention relates to the field of perfumes.
  • it relates to a series of esters of 2,2-dimethyl-propionic acid useful as perfume ingredients.
  • Said esters can be represented by the formula in which the symbol R represents a hydrogen atom or a methyl group and Z represents a bivalent radical of formula
  • a more specific subject of the invention is the use of said compounds of formula (I) as perfuming ingredients, in particular their use in the pure state or as a mixture with one or more ingredients perfuming a solvent or a support.
  • esters see for example S. Arctander, Perfume and Flavor Chemicals, Montclair N.J. 1969, Sections nos. 294, 310, 338, 345, 346, 991 and following 7. Whether they are derived from aliphatic or aromatic acids or alcohols, they are almost all cited in the specialized literature. Very surprisingly, however, nowhere is there any mention of the higher esters of 2,2-dimethylpropionic acid (pivalic acid), more particularly of the esters of araliphatic alcohols and, consequently, of the interest that such compounds could have for the perfume industry.
  • the compounds (I) can therefore be advantageously used as perfuming ingredients, in fine perfumery as well as during the perfuming of products such as soaps, detergents, cleaning products or cosmetic products for example. They can be used, among other things, for the preparation of very diverse perfume compositions, such as fruity, floral, rose, lily of the valley or jasmine compositions, for example, even woody, chypre or fern, to which they contribute to give more richness and roundness. .
  • the compounds (I) can be used both in the pure state and in mixture with one or more of the perfuming ingredients usual in the art, a solvent or a support .
  • compositions for perfumes for example, interesting olfactory effects can be obtained by the use of said compounds (I) at a rate of about 1 to 20, sometimes 30% relative to the weight of said composition, or even 50% or more when preparing bases or hearts for perfumes. Amounts less than 1% may also be used, especially when perfuming products such as soaps or detergents for example.
  • the compounds of the invention have the advantage of being perfectly stable in the various environments of use. Their inertia with regard to the effect exerted by acidic, oxidizing or reducing agents, for example, is such that their use can be extended to the scent of very diverse articles such as soaps, hair sprays, talcs or detergents. In addition, their stability with regard to light is also excellent, hence their good storage life. Finally, the compounds of formula (1) have proved to be biologically harmless under the conditions of use envisaged.
  • a basic perfuming composition was prepared as indicated below:
  • the base thus prepared has a generic flowery odor within which there is a characteristic "thrush" note.
  • This perfuming composition is perfectly suited for perfuming shampoos or hair lotions.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

Les esters de l'acide 2,2-diméthyl-propionique de formule <IMAGE> dans laquelle le symbole R représente un atome d'hydrogène ou un groupe méthyle et Z représente un radical bivalent de formule <IMAGE> sont utilisés à titre d'ingrédients parfumants, notamment pour la reproduction de notes du genre fleuri-fruité Les composés (I) sont pour la plupart nouveaux.The 2,2-dimethylpropionic acid esters of formula <IMAGE> in which the symbol R represents a hydrogen atom or a methyl group and Z represents a bivalent radical of formula <IMAGE> are used as perfuming ingredients, in particular for the reproduction of notes of the floral-fruity genus The compounds (I) are for the most part new.

Description

L'invention se rapporte au domaine des parfums. En particulier, elle a trait à une série d'esters de l'acide 2,2-diméthyl-propionique utiles à titre d'ingrédients parfumants. Lesdits esters peuvent être représentés au moyen de la formule

Figure imgb0001
dans laquelle le symbole R représente un atome d'hydrogène ou un groupe méthyle et Z représente un radical bivalent de formule
Figure imgb0002
 The invention relates to the field of perfumes. In particular, it relates to a series of esters of 2,2-dimethyl-propionic acid useful as perfume ingredients. Said esters can be represented by the formula
Figure imgb0001
 in which the symbol R represents a hydrogen atom or a methyl group and Z represents a bivalent radical of formula
Figure imgb0002

L'invention a plus précisément pour objet l'utilisation desdits composés de formule (I) à titre d'ingrédients parfumants, notamment leur utilisation à l'état pur ou en mélange avec un ou plusieurs ingrédients parfumant un solvant ou un support.A more specific subject of the invention is the use of said compounds of formula (I) as perfuming ingredients, in particular their use in the pure state or as a mixture with one or more ingredients perfuming a solvent or a support.

Elle a également pour objet une composition parfumante contenant un composé de formule (1) de même que, à titre de composés nouveaux, les composés de formule (I) tels que définis ci-dessus, exception faite de celui dans laquelle R représente un atome d'hydrogène et Z le radical de formule

Figure imgb0003
Dans la formule (I) ci-dessus, le symbole R peut être indifféremment localisé en position 2, 3 ou 4 du noyau aromatique.It also relates to a perfume composition containing a compound of formula (1) as well as, as new compounds, the compounds of formula (I) as defined above, except for that in which R represents a hydrogen atom and Z the radical of formula
Figure imgb0003
 In the formula (I) above, the symbol R can be indifferently located in position 2, 3 or 4 of the aromatic nucleus.

L'une des classes de corps odorants les plus intensément exploitées à ce jour est, sans doute possible, celle des esters [voir par exemple S. Arctander, Perfume and Flavor Chemicals, Montclair N.J. 1969, Sections nos. 294, 310, 338, 345, 346, 991 et suivantes7. Qu'ils dérivent d'acides ou d'alcools aliphatiques ou aromatiques, ils sont pratiquement tous cités dans la littérature spécialisée. Fait très étonnant cependant, il n'est nulle part fait mention des esters supérieurs de l'acide 2,2-diméthyl-propionique (acide pivalique), plus particulièrement des esters d'alcools araliphatiques et, par voie de conséquence, de l'intérêt que de tels composés pourraient présenter pour l'industrie des parfums.One of the most intensively exploited odorant classes to date is, undoubtedly possible, that of esters [see for example S. Arctander, Perfume and Flavor Chemicals, Montclair N.J. 1969, Sections nos. 294, 310, 338, 345, 346, 991 and following 7. Whether they are derived from aliphatic or aromatic acids or alcohols, they are almost all cited in the specialized literature. Very surprisingly, however, nowhere is there any mention of the higher esters of 2,2-dimethylpropionic acid (pivalic acid), more particularly of the esters of araliphatic alcohols and, consequently, of the interest that such compounds could have for the perfume industry.

Il a été maintenant trouvé, de façon surprenante, que les composés de formule (1), tels que définis plus haut, présentaient un grand intérêt pour l'industrie et qu'ils pouvaient être avantageusement utilisés à titre d'ingrédients parfumants. Ils développent en effet une note olfactive particulièrement plaisante, de type fleuri-fruité, enrichie selon les cas de tonalités muguet, rose, poire ou bergamote.It has now been found, surprisingly, that the compounds of formula (1), as defined above, are of great interest for the industry and that they could be advantageously used as perfuming ingredients. They indeed develop a particularly pleasant olfactory note, of the floral-fruity type, enriched according to cases of lily of the valley, rose, pear or bergamot.

Les composés (I) peuvent être de ce fait avantageusement utilisés à titre d'ingrédients parfumants, en parfumerie fine tout comme lors du parfumage de produits tels que savons, détergents, produits d'entretien ou produits cosmétiques par exemple. Ils peuvent être entre autres utilisés pour la préparation de compositions parfumantes fort diverses, telles des compositions de type fruité, fleuri, rose, muguet ou jasmin par exemple, voire boisé, chypre ou fougère, auxquelles ils contribuent à donner plus de richesse et de rondeur.The compounds (I) can therefore be advantageously used as perfuming ingredients, in fine perfumery as well as during the perfuming of products such as soaps, detergents, cleaning products or cosmetic products for example. They can be used, among other things, for the preparation of very diverse perfume compositions, such as fruity, floral, rose, lily of the valley or jasmine compositions, for example, even woody, chypre or fern, to which they contribute to give more richness and roundness. .

Pour développer des effets olfactifs tels que ceux définis ci-dessus, les composés (I) peuvent être utilisés aussi bien à l'état pur qu'en mélange avec un ou plusieurs des ingrédients parfumants usuels dans l'art, un solvant ou un support.To develop olfactory effects such as those defined above, the compounds (I) can be used both in the pure state and in mixture with one or more of the perfuming ingredients usual in the art, a solvent or a support .

Lors de la préparation de compositions pour parfums par exemple, des effets olfactifs intéressants peuvent être obtenus par l'emploi desdits composés_(I) à raison d'environ 1 à 20, parfois 30% par rapport au poids de ladite composition, voire 50% ou plus lors de la préparation de bases ou coeurs pour parfums. Des quantités inférieures à 1% peuvent être également utilisées, notamment lors du parfumage de produits tels que savons ou détergents par exemple.When preparing compositions for perfumes for example, interesting olfactory effects can be obtained by the use of said compounds (I) at a rate of about 1 to 20, sometimes 30% relative to the weight of said composition, or even 50% or more when preparing bases or hearts for perfumes. Amounts less than 1% may also be used, especially when perfuming products such as soaps or detergents for example.

Les composés de l'invention présentent l'avantage d'être parfaitement stables dans les différents milieux d'utilisation. Leur inertie vis à vis de l'effet exercé par des agents acides, oxydants ou réducteurs, par exemple, est telle que leur emploi peut être étendu au parfumage d'articles fort divers tels les savons, les laques pour cheveux, les talcs ou les détergents. En outre, leur stabilité vis à vis de la lumière est également excellente, d'où leur bonne durée de stockage. Enfin les composés de formule (1) se sont révélés biologiquement inoffensifs dans les conditions d'utilisation envisagées.The compounds of the invention have the advantage of being perfectly stable in the various environments of use. Their inertia with regard to the effect exerted by acidic, oxidizing or reducing agents, for example, is such that their use can be extended to the scent of very diverse articles such as soaps, hair sprays, talcs or detergents. In addition, their stability with regard to light is also excellent, hence their good storage life. Finally, the compounds of formula (1) have proved to be biologically harmless under the conditions of use envisaged.

Exception faite du pivalate de 1-phényl-éthyle [R = H, Z :

Figure imgb0004
dans la formule I - voir par exemple Chem. Abstr. 66, 55873e (1967)7, les composés (I) sont des composés nouveaux. Ils peuvent être obtenus par estérification des alcools correspondants à l'aide d'acide pivalique, selon les conditions usuelles en chimie organique. Acide et alcools sont pour la plupart des produits du commerce ; les alcools 2-, 3- ou 4-méthyl-benzyliques peuvent être également préparés à partir de l'acide correspondant, après réduction de ce dernier selon les prescriptions de la littérature.Except for 1-phenylethyl pivalate [R = H, Z:
Figure imgb0004
 in formula I - see for example Chem. Abstr. 66, 55873e (1967) 7, the compounds (I) are new compounds. They can be obtained by esterification of the corresponding alcohols using pivalic acid, according to the usual conditions in organic chemistry. Acid and alcohols are mostly commercial products; 2-, 3- or 4-methyl-benzyl alcohols can also be prepared from the corresponding acid, after reduction of the latter according to the prescriptions of the literature.

Les composés les plus représentatifs de la série définie au moyen de la formule (I) sont caractérisés ci-dessous (températures en degrés centigrades).The most representative compounds of the series defined by means of formula (I) are characterized below (temperatures in degrees centigrade).

Pivalate de 2-phényléthyle2-Phenylethyl pivalate

510 g (5 moles) d'acide pivalique en mélange avec 610 g (5 moles) d'alcool 2-phényléthylique, 20 g d'acide p-toluène-sulfonique et 600 ml d'éther de pétrole 80/100, ont été chauffés durant 7 h à reflux dans un réacteur pourvu d'un séparateur d'eau (élimination azéotropique de H20). Après refroidissement et addition de 200 g de glace, le mélange réactionnel a été agité durant 1 h en présence de 200 ml de NaOH à 10%. Après lavage avec H20, séchage (Na2SO4) et distillation sur colonne remplie (hauteur : 40 cm - hélices en verre), on a recueilli 923 g (rendement 89%) du produit désiré, Eb. 840/7 Pa. IR : 2975, 1735, 1490, 1470, 1415, 1380, 1300, 1170, 1050 cm-1; RMN : 1,15 (9H, s) ; 2,9 (2H, t) ; 4,3 (2H, t) ; 7,3 (5H, s) δ ppm ; SM : m/e = 104, 57, 105, 41, 29, 77, 91, 85, 65, 121.510 g (5 moles) of pivalic acid mixed with 610 g (5 moles) of 2-phenylethyl alcohol, 20 g of p-toluenesulfonic acid and 600 ml of petroleum ether 80/100, were heated for 7 h at reflux in a reactor provided with a water separator (azeotropic elimination of H 2 0). After cooling and adding 200 g of ice, the reaction mixture was stirred for 1 h in the presence of 200 ml of 10% NaOH. After washing with H 2 0, drying (Na 2 SO 4 ) and distillation on a filled column (height: 40 cm - glass propellers), 923 g (89% yield) of the desired product, Eb. 84 0/7 Pa. IR: 2975, 1735, 1490, 1470, 1415, 1380, 1300, 1170, 1050 cm -1 ; NMR: 1.15 (9H, s); 2.9 (2H, t); 4.3 (2H, t); 7.3 (5H, s) δ ppm; MS: m / e = 104, 57, 105, 41, 29, 77, 91, 85, 65, 121.

Le procédé ci-dessus a été repris dans des conditions identiques pour la préparation des esters mentionnés ci-après.The above process was repeated under identical conditions for the preparation of the esters mentioned below.

Pivalate de benzyle Eb. 105°/13 x 102 Pa IR : 2970, 1730, 1490, 1470, 1410, 1380, 1290, 1160, 1060 cm-1; RMN : 1,2 (9H, s) ; 5,1 (2H, s) ; 7,3 (5H, s) δ ppm ; SM : m/e : 57, 91, 41, 192 (M+), 29, 65, 108, 77, 119.Benzyl pivalate Eb. 105 ° / 13 x 10 2 Pa IR: 2970, 1730, 1490, 1470, 1410, 1380, 1290, 1160, 1060 cm -1 ; NMR: 1.2 (9H, s); 5.1 (2H, s); 7.3 (5H, s) δ ppm; SM: m / e: 57, 91, 41, 192 (M + ), 29, 65, 108, 77, 119.

Pivalate de 2-méthyl-benzyle Eb. 52°/1 Pa IR : 2995, 1730, 1610, 1490, 1475, 1410, 1380, 1295, 1185, 1050, 980, 865 cm-1; RMN : 1,2 (9H, s) ; 2,3 (3H, s) ; 5,1 (2H, s) ; 7,2 (4H, large s) δ ppm ; SM : m/e = 104, 105, 57, 41, 77, 29, 91, 65, 122, 133.2-methyl-benzyl pivalate Eb. 52 ° / 1 Pa IR: 2995, 1730, 1610, 1490, 1475, 1410, 1380, 1295, 1185, 1050, 980, 865 cm -1 ; NMR: 1.2 (9H, s); 2.3 (3H, s); 5.1 (2H, s); 7.2 (4H, broad s) δ ppm; SM: m / e = 104, 105, 57, 41, 77, 29, 91, 65, 122, 133.

Pivalate de 3-méthyl-benzyle Eb. 62°/1 Pa IR : 2960, 1725, 1610, 1600, 1480, 1460, 1400, 1375, 1280, 1150, 1040, 980, 895 cm-1; RMN : 1,2 (9H, s) ; 2,4 (3H, s) ; 5,1 (2H, s) ; 7,2 (4H, d) δ ppm ; SM : m/e = 105, 57, 206 (M+), 41, 122, 29, 77, 91, 65, 133.3-methyl-benzyl pivalate Eb. 62 ° / 1 Pa IR: 2960, 1725, 1610, 1600, 1480, 1460, 1400, 1375, 1280, 1150, 1040, 980, 89 5 cm -1 ; NMR: 1.2 (9H, s); 2.4 (3H, s); 5.1 (2H, s); 7.2 (4H, d) δ ppm; MS: m / e = 105, 57, 206 (M + ), 41, 122, 29, 77, 91, 65, 133.

Pivalate de 4-méthyl-benzyle Eb. 52°/1 Pa IR : 2970, 1725, 1630, 1525, 1485, 1470, 1405, 1380, 1290, 1160, 1050, 980, 960, 860, 810 cm-1; RMN : 1,2 (9H, s) ; 2,3 (3H, s) 5,1 (2H, s) ; 7,2 (4H, s) δ ppm ; SM : m/e = 105, 57, 206 (M+), 41, 77, 29, 91, 65, 122; 133.4-methyl-benzyl pivalate Eb. 52 ° / 1 Pa IR: 2970, 1725, 1630, 1525, 1485, 1470, 1405, 1380, 1290, 1160, 1050, 980, 960, 860, 81 0 cm -1 ; NMR: 1.2 (9H, s); 2.3 (3H, s) 5.1 (2H, s); 7.2 (4H, s) δ ppm; MS: m / e = 105, 57, 206 (M + ), 41, 77, 29, 91, 65, 122; 133.

Pivalate de 1-phényléthyle Eb. 120°/13 x 102 Pa IR : 2980, 1730, 1480, 1460, 1400, 1370, 1280, 1160, 1040, 1070, 920, 880 cm-1; RMN : 1,2 (9H, s) ; 1,5 (3H, d) ; 5,8 (1H, q) ; 7,3 (5H, s) δ ppm ; SM : m/e = 105, 57, 104, 77, 41, 206 (M+), 29, 122, 85, 63.1-Phenylethyl pivalate Eb. 120 ° / 13 x 10 2 Pa IR: 2980, 1730, 1480, 1460, 1400, 1370, 1280, 1160, 1040, 1070, 920, 880 cm -1 ; NMR: 1.2 (9H, s); 1.5 (3H, d); 5.8 (1H, q); 7.3 (5H, s) δ ppm; MS: m / e = 105, 57, 104, 77, 41, 206 (M + ), 29, 122, 85, 63.

Pivalate de 2-phénoxyéthyle Eb. 55°/1 Pa IR : 2995, 1740, 1610, 1510, 1495, 1470, 1410, 1390, 1300, 1280, 1180, 1100, 1070, 960, 900, 875 cm-1; RMN : 1,2 (9H, s) ; 4,2 (4H, m) ; 7,0 (5H, m) δ ppm ; SM : m/e = 129, 57, 77, 41, 73, 65, 94, 121, 29, 113, 222 (M+), 85, 138.2-Phenoxyethyl pivalate Eb. 55 ° / 1 Pa IR: 2995, 1740, 1610, 1510, 1495, 1470, 1410, 1390, 1300, 1280, 1180, 1100, 1070, 960, 900, 875 cm -1 ; NMR: 1.2 (9H, s); 4.2 (4H, m); 7.0 (5H, m) δ ppm; MS: m / e = 129, 57, 77, 41, 73, 65, 94, 121, 29, 113, 222 (M + ), 85, 138.

Les exemples ci-après illustreront l'invention de manière plus détaillée. Cependant, l'invention ne saurait être réduite à ces seuls exemples.The following examples will illustrate the invention in more detail. However, the invention cannot be reduced to these examples alone.

Exemple 1Example 1

Diverses portions d'une poudre de détergent commerciale, olfac- tivement neutre, ont été séparément parfumées à l'aide des ingrédients suivants (concentrations) :

Figure imgb0005
Various portions of a commercial detergent powder, olfac- neutral, have been separately scented with the following ingredients (concentrations):
Figure imgb0005

Après avoir été soumis à une évaluation olfactive, chacun des échantillons ainsi parfumés a été caractérisé comme suit :

  • a) effet plaisant, diffus, note fleurie de genre bergamote
  • b) odeur fruitée et fleurie, genre bergamote
  • c) odeur douce, rosée
  • d) odeur très fleurie, fruitée, genre rose et poire.
After having been subjected to an olfactory evaluation, each of the samples thus perfumed was characterized as follows:
  • a) pleasant, diffuse effect, floral note of the bergamot genus
  • b) fruity and flowery smell, bergamot type
  • c) sweet smell, dew
  • d) very flowery, fruity, rose and pear-like odor.

Exemple 2Example 2

On a préparé une composition parfumante de base comme indiqué ci-après :

Figure imgb0006
A basic perfuming composition was prepared as indicated below:
Figure imgb0006

La base ainsi préparée possède une odeur fleurie générique au sein de laquelle on distingue une note "muguet" caractéristique.The base thus prepared has a generic flowery odor within which there is a characteristic "thrush" note.

Diverses compositions parfumantes ont ensuite été préparées comme indiqué ci-après, par addition à ladite base parfumante des ingrédients suivants (parties en poids) :

Figure imgb0007
Various perfume compositions were then prepared as indicated below, by adding to said perfume base the following ingredients (parts by weight):
Figure imgb0007

Chacune des compositions parfumantes ainsi obtenues a ensuite été soumise à une évaluation olfactive sous forme de solution à 5% dans l'alcool éthylique et finalement caractérisée comme suit :

Figure imgb0008
Each of the perfume compositions thus obtained was then subjected to an olfactory evaluation in the form of a 5% solution in ethyl alcohol and finally characterized as follows:
Figure imgb0008

Exemple 3Example 3

Composition parfumante de type "fleuri-frais".

Figure imgb0009
Figure imgb0010
 Fragrant composition of the "flowery-fresh" type.
Figure imgb0009
Figure imgb0010

Cette composition parfumante convient parfaitement bien au parfumage de shampoings ou lotions capillaires.This perfuming composition is perfectly suited for perfuming shampoos or hair lotions.

Exemple 4Example 4

Composition parfumante de type "rose rouge".

Figure imgb0011
Perfume composition of the "red rose" type.
Figure imgb0011

Claims (10)

1. Utilisation à titre d'ingrédient parfumant d'un composé de formule
Figure imgb0012
dans laquelle le symbole R représente un atome d'hydrogène ou un groupe méthyle et Z représente un radical bivalent de formule
Figure imgb0013
 1. Use as a perfuming ingredient of a compound of formula
Figure imgb0012
 in which the symbol R represents a hydrogen atom or a methyl group and Z represents a bivalent radical of formula
Figure imgb0013
 2. Utilisation d'un composé de formule (I) selon la revendication 1, pur ou en mélange avec un ou plusieurs ingrédients parfumants, un solvant ou un support.2. Use of a compound of formula (I) according to claim 1, pure or in admixture with one or more perfuming ingredients, a solvent or a support. 3. Composition parfumante, caractérisée en ce qu'elle contient un composé de formule (1) telle que définie à la revendication 1.3. Perfuming composition, characterized in that it contains a compound of formula (1) as defined in claim 1. 4. A titre de composé nouveau un composé de formule (I) telle que définie à la revendication 1, exception faite de celui dans laquelle le symbole R représente un atome d'hydrogène et Z le radical de formule
Figure imgb0014
 4. As a new compound a compound of formula (I) as defined in claim 1, except for that in which the symbol R represents a hydrogen atom and Z the radical of formula
Figure imgb0014
 5. Pivalate de benzyle.5. Benzyl pivalate. 6. Pivalate de 2-méthyl-benzyle.6. 2-Methyl-benzyl pivalate. 7. Pivalate de 3-méthyl-benzyle.7. 3-Methyl-benzyl pivalate. 8. Pivalate de 4-méthyl-benzyle.8. 4-Methyl-benzyl pivalate. 9. Pivalate de 2-phényl-éthyle.9. 2-Phenylethyl pivalate. 10. Pivalate de 2-phénoxyéthyle.10. 2-Phenoxyethyl pivalate.
EP81201262A 1981-01-16 1981-11-12 2,2-dimethyl-propionic acid esters, their use as perfuming agents and composition containing one of them Withdrawn EP0056500A3 (en)

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CH271/81 1981-01-16
CH27181 1981-01-16

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EP0056500A2 true EP0056500A2 (en) 1982-07-28
EP0056500A3 EP0056500A3 (en) 1982-11-17

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4524021A (en) * 1983-05-05 1985-06-18 International Flavors & Fragrances Inc. Perfumery uses of esters of phenyl alkanols
WO2005110967A1 (en) * 2004-05-12 2005-11-24 Symrise Gmbh & Co. Kg 3-methylbenzyl-isobutyrat
US7494967B2 (en) 2004-05-12 2009-02-24 Symrise Gmbh & Co. Kg 3-methylbenzyl-isobutyrate
EP2065360A2 (en) 2004-05-12 2009-06-03 Symrise GmbH & Co. KG 3-methylbenzyl isobutyrate
US7638479B2 (en) 2004-05-12 2009-12-29 Symrise Gmbh & Co. Kg 3-methylbenzyl-isobutyrate
EP2065360A3 (en) * 2004-05-12 2012-02-29 Symrise AG 3-methylbenzyl isobutyrate
US8363787B2 (en) 2009-03-25 2013-01-29 General Electric Company Interface for liquid metal bearing and method of making same
WO2010140076A1 (en) * 2009-06-04 2010-12-09 Firmenich Sa Phenol ester as perfuming ingredient
CN102458349A (en) * 2009-06-04 2012-05-16 弗门尼舍有限公司 Phenol esters as perfuming ingredients
CN102458349B (en) * 2009-06-04 2013-09-25 弗门尼舍有限公司 Phenol ester as perfuming ingredient
US8648032B2 (en) 2009-06-04 2014-02-11 Firmenich Sa Phenol ester as perfuming ingredient

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